Organic & Biomolecular Chemistry Blog

Work from Srinivas Hotha at the Indian Institute of Science Education & Research, and colleagues at the National Chemical Laboratory (Pune, India) features on the front cover of Issue 17. Their paper describes the efficient preparation of glycosylated amino acids using propargyl orthoesters as glycosyl donors, via gold-catalysis.

Are your interests in carbohydrate chemistry, or peptide and glycopeptide chemistry? Then this article is for you!

Facile synthesis of unusual glycosyl carbamates and amino acid glycosides from propargyl 1,2-orthoesters as glycosyl donors
Ashif Y. Shaikh, Gopalsamy Sureshkumar, Debasish Pati, Sayam Sen Gupta and Srinivas Hotha
Org. Biomol. Chem., 2011, 9, 5951-5959
DOI: 10.1039/C1OB05056G

As with all our cover articles, this paper is free to access for 6 weeks – why not download it today.

View the issue here

On the front cover of this issue is work from Debendra Mohapatra at the Indian Institute of Chemical Technology, together with colleagues at Hyderabad University and King Saud University on the ring-closing metathesis based synthesis of the macrolactone core of amphidinolactone A.

The convergent synthesis achieved the macrolactone core in 32% yield and demonstrated the steric hinderance resulting from protecting groups in the RCM reaction.  PMB (p-methoxybenzyl ether) protecting groups on the macrolactonization precursor prevented the RCM reaction from proceeding, but  simple de-protection to the subsequent diol achieved the 13-membered lactone ring system present in amphidinolactone A in 76% yield.  Further work to incorporate the the RCM reaction into the total synthesis of amphidinolactone A is ongoing.

Ring-closing metathesis (RCM) based synthesis of the macrolactone core of amphidinolactone A
Debendra K. Mohapatra, Manas R. Pattanayak, Pragna P. Das, Tapas R. Pradhan and J. S. Yadav
Org. Biomol. Chem., 2011,
DOI: 10.1039/C1OB05335C

View the rest of the articles in Issue 16

Work from Asish K. Bhattacharya (National Chemical Laboratory, India) and co-workers features on the front cover of Issue 15.  Their paper describes the FeCl₃ catalysed four-component condensation of diamines, acetone and phosphites in the presence of molecular sieves to yield benzodiazepinyl phosphonates which demonstrate protease inhibition activity against clostripain.

An efficient synthesis of benzodiazepinyl phosphonates as clostripain inhibitors via FeCl3 catalyzed four-component reaction
Asish K. Bhattacharya, Kalpeshkumar C. Rana, Dnyaneshwar S. Raut, Vaibhav P. Mhaindarkar and Mohamad I. Khan
Org. Biomol. Chem., 2011, 9, 5407-5413
DOI: 10.1039/C0OB01102A

On the inside front cover we have work from Boris Vauzeilles (CNRS) et al. on the synthesis of neoglycoconjugates as glycosidase inhibitors through click connection of the iminosugar deoxynojirimycin and functionalised adamantanes.

Selection of the biological activity of DNJ neoglycoconjugates through click length variation of the side chain
Nicolas Ardes-Guisot, Dominic S. Alonzi, Gabriele Reinkensmeier, Terry D. Butters, Caroline Norez, Frédéric Becq, Yousuke Shimada, Shinpei Nakagawa, Atsushi Kato, Yves Blériot, Matthieu Sollogoub and Boris Vauzeilles
Org. Biomol. Chem., 2011, 9, 5373-5388
DOI: 10.1039/C1OB05119A

Both articles are free to access for 6 weeks, so why not take a look? You can also view the rest of the issue online here

On the cover of Issue 14 is work from Dario Pasini and colleagues at the University of Pavia.  They have designed a new route to the synthetically challenging cyclophane, [2.2]cyclophanediene.   By using a Pummerer rearrangement of the [3.3]dithiacyclophane starting material, followed by sulfur extrusion the group were able to demonstrate the applicability of this mild and high yielding route.

For the full details download the article – it’s free to access for 6 weeks:

Mild preparation of functionalized [2.2]paracyclophanes via the Pummerer rearrangement
Matteo Montanari, Alberto Bugana, Arvind K. Sharma and Dario Pasini
Org. Biomol. Chem., 2011, 9, 5018-5020
DOI: 10.1039/C1OB05319A

View the issue here

Check out the cover articles in Organic & Biomolecular Chemistry Issue 11.

The outside cover features work by Michael Doyle and colleagues  at University of Maryland. They talk about catalytic C-H insertion processes in comparison with other approaches for the synthesis of selected synthetic targets, lactones and lactams, which have been of biological or medicinal interest. It is a very interesting and original review article. Read more at

Intramolecular catalytic asymmetric carbon–hydrogen insertion reactions. Synthetic advantages in total synthesis in comparison with alternative approaches
Michael P. Doyle, Maxim Ratnikov and Yu Liu
Org. Biomol. Chem., 2011, 9, 4007-4016
DOI: 10.1039/C0OB00698J

The inside cover represents how Aminoglycoside acetyltransferase AAC(6’) belonging to the aminoglycoside-modifying enzymes (AMEs) does not deactivate the 6’-N-glycinyl tobramycin which attacks the bacterial ribosome (green arrow). In contrast, the parent aminoglycoside tobramycin cannot pass through bacterial resistance mechanism (red arrow).
You can read more about this article by Micha Fridman, Sylvie Garneau-Tsodikova and co-workers at Michigan and Tel Aviv at

Assessment of 6′- and 6′′′-N-acylation of aminoglycosides as a strategy to overcome bacterial resistance
Pazit Shaul, Keith D. Green, Roi Rutenberg, Maria Kramer, Yifat Berkov-Zrihen, Elinor Breiner-Goldstein, Sylvie Garneau-Tsodikova and Micha Fridman
Org. Biomol. Chem., 2011, 9, 4057-4063
DOI: 10.1039/C0OB01133A

Both articles are FREE to download until the end of June.

Leo Radom and collaborators in Australia and Switzerland present in this paper a thorough computational study, which correlates with experimental data, of the stability of a very large series of multiply-substituted carbon-centered radicals. They look at the stabilization and interaction energies and the deviations from additivity of RSEs.

The cover image depicts how the stabilities of multiply-substituted carbon-centered radicals are compared with the stabilities of their monosubstituted components. The factors that influence the effect of substituents on such a comparison are discussed.

This article will be included in the OBC special issue in memory of Athel Beckwith: Free Radical Chemistry. Coming soon.

Effect of substituents on the stabilities of multiply-substituted carbon-centered radicals
Ambili S. Menon, David J. Henry, Thomas Bally and Leo Radom
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB05196B

Why do certain DFT methods give good results for ring-opening reactions while others do not?

Gino DiLabio and Iain Mackie at University of Albaerta, in Canada, try to answer this question in this timely paper on radical clock reactions.

You can read it for free until the end of May.

This paper will be included in the special web themed issue on radical chemistry in memory of Athel Beckwith that will be published soon. Keep an eye on it!

Ring-opening radical clock reactions: many density functionals have difficulty keeping time
Iain D. Mackie and Gino A. DiLabio
Org. Biomol. Chem., 2011, 9, 3158-3164
DOI: 10.1039/C0OB01246G

Atsushi Ikeda and colleagues describe in this paper, which is the outside cover of OBC Issue 8, how the addition of small amounts of lipids bearing a π-moiety can help the migration of hydrophobic C₇₀ into the hydrophilic liposome surface.
The delivery of fullerenes C₇₀ into liposomes could have interesting applications in drug delivery. 

Read more about the mechanism of how fullerenes are incorporated into the lipid structures in this article which is free to access for 6 weeks!

Formation and regulation of fullerene-incorporation in liposomes under the phase transition temperature
Atsushi Ikeda, Yoshihiko Kawai, Jun-ichi Kikuchi, Motofusa Akiyama, Eiji Nakata, Yoshihiro Uto and Hitoshi Hori
Org. Biomol. Chem., 2011, 9, 2622-2627
DOI: 10.1039/C0OB01030H